Avery, Mitchell A. published the artcileStructure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates, Formula: C3H5F3O, the publication is Journal of Medicinal Chemistry (2002), 45(19), 4321-4335, database is CAplus and MEDLINE.
On the basis of earlier reported quant. structure-activity relationship studies, a series of 9β-16-(arylalkyl)-10-deoxoartemisinins, e.g. I, were proposed for synthesis. Several of the new compounds were synthesized employing the key synthetic intermediate II. In a second approach, the natural product (+)-artemisinic acid (III) was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogs. Under a new approach, we developed a one step reaction for the interconversion of artemisinin into artemisitene (IV) that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of IV in good yield. The lactone carbonyls were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF3-etherate/Et3SiH) to afford the desired corresponding pyrans. Six addnl. halogen-substituted aromatic side chains were installed via IV furnishing the bioassay candidates. The analogs were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were addnl. tested in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity. Of these, two were chosen for pharmacokinetic evaluation, V and VI.
Journal of Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Formula: C3H5F3O.
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